反应详情

温度

100 °C

To a solution of ethyl 3-(5-(bromomethyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (100 mg, 0.187 mmol) in toluene (5 mL) was added (4-chlorophenyl)boronic acid (32.1 mg, 0.205 mmol) and aq. Cs2CO3 (1 M, 0.28 mL). The reaction was degassed under nitrogen gas (3×) then Pd(PPh3)4 (10 mg) was added. The reaction was heated at 100° C. for 18 h, cooled to RT then diluted with EA (10 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (4:1 to 2:1) to give ethyl 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (51 mg, 48.1% yield) as a yellow solid. LCMS: MH+ 567 and TR=1.710 min.

1. customThe reaction was degassed under nitrogen gas (3×)
2. additionPd(PPh3)4 (10 mg) was added
3. temperaturecooled to RT
4. additionthen diluted with EA (10 mL)
5. washThe organic layer was washed with brine (5 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to a residue which
8. customwas purified by chromatography
9. washeluted with PE/EA (4:1 to 2:1)